Methyl iodide → (S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester

HRID 2256450

반응식

HRID 2256450 반응식
[C:1]1(=[O:20])[N:5]([C@@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[C:7]([OH:9])=[O:8])[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[C:21](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.C(OCC)(=O)C>[C:4]1(=[O:15])[N:5]([C@@H:6]([CH2:10][CH2:11][CH2:12][CH2:13][OH:14])[C:7]([O:9][CH3:21])=[O:8])[C:1](=[O:20])[C:2]2=[CH:19][CH:18]=[CH:17][CH:16]=[C:3]12

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acid

생성물 1

HCID 10859253(S)-2-Phthalimido-6-hydroxyhexanoic acid, methyl ester수율 196%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A slurry of (S)-2-phthalimido-6-hydroxyhexanoic acid (3.752 g., 13.5 mmol.) and cesium carbonate (2.178 g., 6.7 mmol.) in dimethylformamide (44 ml.) was treated with methyl iodide (3.0 ml., 6.84 g., 48.2 mmol.). After stirring at room temperature for 2 hours, the mixture was diluted with ethyl acetate and washed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine, then dried (sodium sulfate), filtered and stripped to give the title product as a colorless oil (3.825 g.). The oil was homogeneous by TLC (1:1-acetone:hexanes) Rf =0.37.

후처리

  1. washwashed successively with water containing a small amount of sodium bisulfite, water, 50% saturated sodium bicarbonate, and brine
  2. dry with materialdried (sodium sulfate)
  3. filtrationfiltered

출처 및 근거

ORD 기록
ord-d42514b9d49944c788fa12e6bc81e4a0
출처 데이터셋
uspto-grants-1997_08
특허 번호
US05654294

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